TeNN is an acronym for tetranitronaphthalene. There are actually several isomers of TeNN, we are primarily concerned with 1,3,6,8-tetranitronaphthalene as it forms in abundance over the 1,2,4,6-; 1,2,5,8-; 1,2,6,8-; 1,3,5,7-; 1,3,5,8-; and 1,4,5,8-tetranitronaphthalenes. A mixture of isomers is bound to occur, though. TeNN is a very powerful and quite stable high explosive compound. It is actually slightly more powerful that TNT and just as stable. This explosive is superb because of its primary ingredient naphthalene. Naphthalene is the chemical name for moth balls, it is cheap, easy to get, not to hazardous, and sold in a store near you. I keep waiting for the government to ban it, or some environMeNtaList whacko to launch a save the moths campaign to ban it. The only drawback to TeNN is the possibility of side reactions reducing the yield during synthesis. Rapid heating of TeNN will cause it to explode, but slow heating will only cause decomposition. This lab uses concentrated sulfuric and nitric acids which are not so common, but still obtainable. Making TeNN is a multi step synthesis, first making mononitro then 1,8-dinitronaphthalene.
|ethyl alcohol||2000-mL beaker|
|nitric acid||stirrer/stirring rod|
Prepare a mixture of 64 g of powdered naphthalene with 105 mL of water in a 1000-mL beaker. Slowly add 160 mL of 95% sulfuric acid to the beaker then add 81 mL of 70% nitric acid. Stir this mixture occasionally and allow it to cool to room temperature. During a 3 hour period, slowly add with stirring 150 g of powdered naphthalene to the acid mixture. The temperature will rise, regulate the addition of the naphthalene to get the temperature at 50 °C by the end of the addition time. After all of the naphthalene has been added, continue stirring and heat the beaker to 55 °C for several minutes then stop stirring and allow the mix to cool. Some mononitronaphthalene should crystallize on the surface of the beaker.
Prepare a second nitrating mixture by putting 300 mL of 53% sulfuric acid in a 1000-mL beaker. Cool the acid to 25 °C by placing in a salt-ice bath. Add 152 g of potassium nitrate to the acid while stirring rapidly. Remove the mononitronaphthalene from the previous reaction and crush it up, add it in small bits while stirring to the mixture, maintain the temperature between 38 °C and 45 °C. The addition should require about 1 hour, do not allow the temperature to go over 45 °C at any time during the addition. After the addition, continue stirring and heat the beaker to 55 °C until the formation of dinitronaphthalene crystals begin. Filter the contents of the beaker on an acid filter to collect the crystals of dinitronaphthalene that should have formed. Wash the crystals with six portions of cold water and allow them to dry. Dissolve the dry crystals in boiling acetone. Filter this solution while hot to remove any undissolved impurities, collect the filtrate and allow it to cool by placing in a salt-ice bath. Filter to collect the pure crystals of dinitronaphthalene. Collect the acetone filtrate from this filtering, boil it to reduce the volume by half, and cool in a salt-ice bath. Again filter to collect a second crop of dinitronaphthalene, add these crystals to the previous and allow them to dry.
Prepare the final nitrating acid mixture by slowly adding 750 mL of 100% sulfuric acid to 750 mL of 100% fuming nitric acid in a 2000-mL beaker. Cool the acid mix to below 20 °C with a salt-ice bath. Once below this temperature, slowly add with stirring the dry dinitronaphthalene from the previous reaction while maintaining the temperature at 20 °C during the addition. After the addition, slowly heat the mixture to 80 °C over a 1 hour period (1 degree higher every minute) then hold the temperature at 80-90 °C for 3 hours more. Allow the mixture to cool then filter on an acid filter to collect the crystals of TeNN that should have formed. Collect the filtrate and drown it in ice water to precipitate additional crystals of TeNN. Filter to collect these crystals and combine them with the other crystals. Wash the crystals with several portions of water then add them to 95% ethyl alcohol. Allow the crystals to dissolve, then cool in a salt-ice bath to recrystallize the now pure TeNN. The pure crystals can be filtered to collect them and dried by heating on a steam bath.
You will need a graduated cylinder for measuring liquids, a stirring rod or magnetic stirrer for mixing, and a thermometer to monitor the temperature for these procedures.
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